How to connect with your market to find a painful problem

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Last post, I showed you how I chose my market.

The next step reach out to them so you can ask them questions to find a painful problem that will lead you to building your first product.

In this post you will learn my approach to reaching out to a market. It’s not the only way, but it’s what worked for me.


When you are going to reach out to your market, the first thing you should do is think about where they are and what they are doing all day. For me, I knew physical therapists were busy with patients all day, so calling them and interrupting when they are with a patient is not a good idea. Email was the obvious first choice. Other markets that are manning the phones all day, like car dealers, might be easiest to cold call. Thinking this way is a great start, but next you want to take action and make some calls or send some emails to see what works. You won’t know what works until you test things out… I’ve seen people have success with cold calls, emails, LinkedIn messages, and more… That said, I’m going to focus on email in this post because it’s what I focused on and is what’s proven to work the best in most cases.


There are 2 email strategies that I use. The first was sending out 50 emails at a time using a template. This works really well and is proven… A lot of you know about it using the “strange question” email. The second, was sending one email at a time, and personalizing each one. This approach is my favorite.  It creates better relationships, is more personal, and has gotten me >80% response rate. This is the method I’ll go through here…

Create your list

There are loads of different ways to create email lists. I’m not going to get into all of them here. What worked for me, was simply searching on google maps for my market name, visiting each persons website, and gathering personal email addresses ( not

I did this a few times myself until I had it down then I hired an assistant on ODesk to do it for me. I only had about 2 hours per day to work on this, so outsourcing this process enabled me to connect with far more people, faster.

Write the email

Your email should be very simple.  Here are a few rules.

  1. Always address a person directly.  If you don’t, you are unlikely to get a response.
  2. Keep it short (under 5 sentences)
  3. Include something personal about them on the first line of the email.
  4. Make it easy to reply by asking one simple question.
  5. Adjust your email as you learn more about your market to improve open and response rates. Test, adjust, repeat.

Here is one email that worked well for me…

Subject: Can you help me [first name]?

Hey Brian,

Read your blog post on the xyz blog and thought it was great, so I felt the need to reach out.

My name is Carl and I am a software entrepreneur doing research on [market name]. My goal is to learn about the biggest pains you have running your business and to solve a big problem that will make your life easier.

What are your biggest frustrations with managing your business?

Love to hear back from you, even if it’s only one sentence.

Be well,


Your Name
Your Phone Number
Link to your LinkedIn account

The process

Each evening I took a list of about 50 people and uploaded them into ToutApp (a service that helps you send and track your emails). I’d schedule them to go out the following morning just before 9am in their local timezone.  Then I’d wake up to an inbox full of a few responses.  For people that do not respond, I’d look at Tout to see who opened the emails and followup with another email a week later basically just asking if they got the original email.  This doubles the response rate.

Turn it into a habit

Once I got this process going I quickly turned it into a habit. My good friend Josh Isaak talks about the 20 mile march. It’s hugely important to create this type of routine because this is not an overnight process and without forming the routine, I would have burnt myself out.

For me it was to schedule 50 emails to go out each night to go out the following morning. Then I’d write responses, schedule and have calls each morning before work. I was on fire during this period. And I have no doubt it’s because I created this routine for myself.

Hit me up with any questions you have and I’ll answer them all.

Also, tell me what you’d like to learn more about in the comments and I’ll make that the next post.


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  • amul jeff

    Good stuff here Carl.. Keep this sort of actionable stuff coming!!

    • Carl


  • Jason Griffing

    Great stuff. Love the example scripts, as well as the tips on breaking it down to small pieces.

    Keep it up. I’d be really interested in learning about your wire framing / early development process.

    Also perhaps some advice on choosing a developer to work with. I know you said you ended up partnering with a friend. But for someone who doesn’t have any development experience, where to start…?

    Keep it up!

    • Carl

      Thanks Jason.

      I will definitely share a post on wireframing and early dev. I LOVE wireframing and turning it into a clickable prototype I can use to get feedback and eventually sell.

      Advise on finding a developer. For sure. My friend Ed Halloway and I just gave a presentation on this to the Foundation alumni in Boulder last weekend. Pretty sure that session was recorded so Ill see if we can share that.

      • Jason Griffing

        Awesome. I’ll be sure to stay tuned!

      • topsoloja

        Interested in this too.

  • Ryan Leavitt

    Hi Carl,
    I heard your story on SPI and was truly inspired. I know in the interview you said you used a wire frame software, but i can not remember what it was. Can you jog my memory? Also I have a pretty good following in my industry and really think this could take my business to the next level. Anyways thanks for sharing your story I with you success with your business!

    • Carl

      Hey Ryan – My favorite wireframing software is keynote with keynotopia ( If you don’t use a mac I think you can use keynotopia with powerpoint as well.

  • Chris Walker

    Hi Carl,

    I love what you’ve shared so far. The scripts are especially helpful!

    I have a couple of questions if that’s ok:

    Did you focus on emailing businesses that were nearby (so that face to face meetings would be possible?) or at least in your timezone? I’m assuming not as you’ve said that you’d wake up to an inbox full of responses, but am wondering whether this was a consideration at all.

    If you were doing most of your calls before work, did you find it easier to set up calls with businesses in other timezones (where it was during their working day in your 6-8am slot)?

    Thanks for sharing


    • Carl

      Hey Chris,

      You are right. It was easiest for me to focus on the east coast because they were up and already working during the only time I had in my day for calls. I’m living in SF and I grew up in PA. I started with PA cause I thought it would be cool to talk to people near where I grew up.

      Eventually, most of my calls came from referrals though… People liked what I was doing so at the end of the calls when I said “Do you know of anyone else that’s smart and fun to talk to like you that would enjoy a conversation with me like this?” They’d usually hook me up with a few friends… And sometimes even a whole list of people…

      • Chris Walker

        Thanks Carl – that makes a lot of sense. That’s a great question to end on. I’ll add it to my list!

  • Dale Henning

    Carl, thanks so much for explaining your email strategy and your mindset behind it…it’s a BIG help! I’m in the middle of extracting ideas with my target niche, and I’m going back to my oDesk VAs with a revised process based on what you described in your article. I’d also love to hear how you came up with mapping out the pains you found during the calls…basically how you went from having all the data learned from the calls to deciding on software features. I think you touched briefly on this in your speech on website.

    I would also like to hear about the demo you had created and how it helped beyond just creating the “info-pack” as a selling tool. Thanks for putting yourself out here and for providing such awesome material. You are pure inspiration to me.

    • Carl

      Hey Dale,

      Dane teaches that if you understand the pain people will automatically assume you have a great solution. All of the research done talking to customers is ideal for copywriting. But I just kind of put that together with my own knowledge of product development (which I’ve done for years) to connect all types of tangible and emotional pain with features… I guess thats just something I came up with along the way… This is something Ill be teaching in to next years foundation class.

      Jason (below) also asked for more info on wireframing and the clickable demo. So I guess that’s 2 votes for that. Happy to show you guys my process for that in a post. But try not to get too ahead of yourselves here… It’s best to stay laser focused on whatever your next step is. Otherwise you just end up reading and learning too much without actually taking action…

      Thanks for all the kind words and as long as you guys are taking action, Ill be here to help you through it.

      • Dale Henning

        Thanks, Carl!

  • Mark Barron

    Hi Carl,
    I really enjoyed this post as well as the others that you have shared regarding your new business. I do have a question though on your approach to e-mailing your market. Did you send this from your personal e-mail account (i.e. gmail) or were you sending it from your own domain name. I feel like something with a domain extension other than looks more professional, but then again, I may be focusing on the wrong things and perhaps these potential clients won’t even care as much as I think they would.

    Looking forward to hearing back. Keep up the great work!

    • Carl

      Hey Mark,

      Good question. I used my personal email account. At the time I didn’t have another domain.

      And yes I do think this would be kind of something not very important to focus on… Pretty sure you will get fine results with a personal account.

      Give it a shot and let me know how it goes.


      • Mark Barron

        Thanks for the response Carl. I will give it a shot and let you know how it goes.

  • Bobby Hewitt – CreativeThirst

    Hi Carl,
    Thanks for sharing.
    I’m finding it difficult finding emails and names of decision makers on their websites. What strategies did you use to get that data?

    • Carl

      Hey Bobby,

      I’ll do another quick post on this soon. Maybe tomorrow.

      It will cover how to guess emails using rapportive, how to search for them on google, and a few other tricks I’ve used.

      • Brent Giesler

        +1 for that, Carl. I think that’s a big stumbling block for me, too.

        • Jim Piety

          I, too, am struggling in that same regard. Much appreciated Carl!
          You rock!

  • Pong Li

    This is brilliant!!! God bless you Carl!

    • Carl

      Thanks Pong!

  • Patricia O’Sullivan

    Really valuable information. Thank you Carl. I am just starting on emails now having completed 10 telephone interviews which have given me a better understanding of my chosen market niche. Your post and email just saved me a lot of time and the tip about Google maps was invaluable.

    How many of idea extraction interviews do you think should be completed before starting to work on designing the initial possible solution?

    • Carl

      As many as it takes to get at least 3 people to say they would pay for a solution to the same pain you extracted. Thats enough to start on your UI design.

      Then at least 3 (preferably more) to pre-pay for your solution based on the UI you design.

      • Patricia O’Sullivan

        Thanks Carl. I have interviewed 13 people now and all except one have the problem(s). I now have absolutely no doubt that there is a problem and what is needed to fix it but I don’t want to stall designing anything just yet because every person I speak to has some different nuance that is significant and will influence the design and value-add. One other big reason is that the more ‘friends’ I make now during research the more potential pre-sales I can hope for. I know from experience that people will buy-in better if they think they were involved in what was produced so I am playing that card too.

        Thanks for saying the 3 though because I wondered if I needed 30 or 50 people all saying the same thing – I might do that anyway just for the hell of it 🙂

        I appreciate your support.

  • Chris Thorne

    Hey Carl,

    Thanks again for a very helpful post. Can I ask whether you found any difference between reaching out to small businesses vs bigger ones in your market?


    • Carl

      Yep there is a huge difference in approach and results.

      I found the people running bigger businesses tend to… run there business like a business.

      You want that when you are finding problems because they pay more attention to the processes and improvements.

      Eventually I only targeted the bigger businesses or rockstars in the industry…

      The business doesnt have to be big for it to be run by a rockstar, but if it is, it’s a good indication that someone smart is running it… So its a good way to find the best people to talk to.

      • Chris Thorne

        HA – typical. Here’s me thinking I’ll start small. No staying in my comfort zone on this occasion!

  • Niall Doherty

    Love this, Carl. Just hired someone on oDesk to help me collect leads. Will definitely try personalizing the emails as you suggest. Cheers!

    • Carl

      Awesome Niall!

  • Brian Graves

    I started with your script, modified it to my needs, and emailed 8 businesses last night. I only had 30 minutes to work…but wanted to start the 20 mile march with 1 small step 🙂 I also used the ToutApp to schedule the emails for delivery at 9AM their local time today, so I’m eager to see what happens. I am planning to gather more emails (I have a great process for that) and send out 30 or more each day for the next week or so.

    Thanks for the crystal clear directions and inspiration!

    • Carl

      Awesome let us know how it goes.

      PS – If you don’t get a response out of 8 emails don’t be discouraged. The best I’ve seen for IE was like 11/100.

      • Brian Graves

        I already got one message back from a very enthusiastic prospect! We are going to chat early next week. I’m hoping to get another few lined up.

  • Kevin McCoy

    Thanks so much for this post and your intereviews on the Starting From Nothing podcast. I have a lot of the same limiting beliefs you do…it was like hearing me talk, kinda spooky. I appreciate you being open and sharing your story.

    • Carl

      Of course! Hope it helps you.

  • Eric Kruep

    Hey, Carl! Thanks for being such an inspiration, and sharing what works well. You are very appreciated (as you can tell by all the comments, right?),

    I am wondering how you knew the “personal detail” to add at the beginning of your email, especially since you were batching so much? Did your VA track down there details, and if so, what was the VA looking for (blogs, other publications,etc)?

    Thanks in advance, Carl!

    • Carl

      Hey Eric,

      Sorry for the delayed answer here… Yes, at first I’d have the VA put the info into a spreadsheet for me so I could review it.

      I trained her to obtain it by searching for the persons name, looking at the website, looking for publications, etc… There is always something out there… Then she’d suggest things…

      After a while, she was able to do that on her own with little guidance.


  • Robert Moutal

    Hey Carl. I’ve been following your technique outlined here and it’s giving me great results. I hired an amazing VA who’s putting together a list of 100 names in 5 categories (while I determine where I want to focus). I’ve been sending 50 emails a day (with different versions of my email to see which one converts better).
    My problem is that I now have 10 people ready to talk to me within then next couple of days and I want to strike while the iron’s hot!!! (Yeah, I know, great problem to have). How did you deal with that and your daily schedule? Did you have a similar problem? Cheers and thanks for your help!

    • Carl

      Ha. Good problem dude. Yes I had that. If you need to, slow your emails down and schedule them out.

      You’ve accomplished what I try to help all my coaching clients with. Build a routine and be able to turn on and off the firehose when you need more or less. It should be that effortless so you can focus on your calls.

      • Robert Moutal

        Thank you, my man! Once again, very helpful.

  • Peter

    Hey Carl,

    Thanks for this, especially the email template! I modified the email that I had been sending out and am getting a much better response rate.

    How do you handle people that want something custom? Is it best to try and move into other areas, or do you explore whatever it is they want customized and then try to come up with a solution that would work for them and others.

    (Also, I just realized that the custom stuff could also potentially be useful for “niche-ing” down your product if you’re in a big niche. Find out if the custom solution could be turned into be a solution for a subset of the big niche. If the subset is big enough, it should still work, plus your marketing will already be more targeted!).

    Any thoughts?

    • Carl

      Nice and glad you are getting success with the template.

      Custom stuff… Listen and talk to more people. Most people believe they need something custom but when you talk to enough people, patterns emerge. Identify those patterns and you will find a solid product idea.

      • Peter

        Awesome. Thanks!

  • Katie McCabe

    Carl, your website is incredibly helpful. I’m on the waiting list for the Foundation but it sounds like it is too late to get in this year, so I am so happy that you are here to help. I have started sending out initial emails (after doing some idea extraction phone calls with friends–which I would recommend as a first step to anyone who is intimidated about their first few IE sessions) and I have a question for you. For businesses that have more than one partner/owner, do you suggest emailing all of them or does that make it seem more like spam? Thanks so much!

    • Carl

      Thanks Katie! Yeah mail both. No harm.

      • Katie McCabe

        Thanks Carl!

  • Katie McCabe

    Hi Carl,

    I’m in the middle of the “connecting with your market” stage, and I just wanted to pipe in and say that I am starting to have fun! It really is about connection. I haven’t gotten too many people to agree to an idea extraction phone call yet, but I’ve been having some fun email exchanges regardless. I “met” (over email) the sister of a mystery writer (a genre I’m a huge fan of, so I just finished his first book), a woman who has similar social change interests (and who passed along my web site to some of her colleagues…it never occurred to me that this process might help women around the world!), and a fellow world traveler. Who would have thought?

    Someone already asked a similar question below, but I just wanted to see if you have any more insight into how to get the people who answer your email (maybe even a couple of back-and-forths) to make the leap to a phone call? My target market is full of busy people (time is money!) and I’m not quite getting to the next step, usually. Also, I think you said in an interview that you had about 30 idea-extraction phone calls. Approximately how many people did you have to email to get to that number of phone calls (I’m trying to make myself feel better here, ha!).

    Thanks again for ALL you are doing to help us,

  • Henrik Jørgensen

    Hey Carl. Great post. Love what you’re sharing.

    I have a question about the LinkedIn profile you’re sharing in the email. At the time you were sending out these emails, I assume you were still at Tesla and didn’t have a company yet. Is that also what your LinkedIn profile told or did you create a separate profile or add something else to your existing profile?

  • Assya Moustaqim-Barrette

    Hey Carl! thanks for the great post. My target market is the dental industry. Say I cannot reach office managers directly, how would you recommend using the publicly available “” type emails? Thanks.

  • Benjamin Pyle

    Hi Carl, I saw on the email template that you gave your LinkedIn profile. Did you have anything on that that stated you were an entrepreneur before you started calling people? I am at the point where I am going to be sending out emails soon, but I wanted to be prepared to answer people if I introduce myself as an entrepreneur and they ask what my entrepreneurial experience is. Obviously I don’t want to say..”Uh well I am just starting out” but I wanted to know if you ran into this when you started contacting people. Thanks!

  • Ryan Hoek


    How many emails did you send out every day if you customized them to each individual person?